First Date

I pulled up to the address she had provided at 7:30 on the dot. I had no doubt she would have waited for me, but punctuality was a habit of mine. The apartment complex she lived at was a familiar sight. The same kind of cramped apartment buildings were common throughout the city, where two or three bitches packed into the tiny units. There was a reason this slut was so eager to get a man.

And indeed, eager she was. She came out of the door right away, clearly having waited anxiously for my arrival. The whore was even more beautiful dolled up than she had been in her workout clothes. A form-fitting black crop-top hugged her tits deliciously, and the lacy yellow thong she was wearing certainly complemented her form as well. Paired with stilettos and a little yellow purse, it was quite the ensemble.

I popped open the door to my Rolls Royce, allowing her to take a seat. She seemed quite impressed by the fancy car; I was even more of an opportunity than she had realized. Then she did a double take at my face. “Oh my god! You’re Leonardo Segeste!” She exclaimed.

I flashed her a smirk. “Indeed I am. I don’t think I ever caught your name?”

“I’m Mila.”

“It’s great to see you, Mila. Love the outfit, by the way.” Only the faintest of blushes crept across her cheeks. It was hardly the crudest of compliments compared to what I was sure she had heard in the past. “Why don’t you climb in? I’m famished.”

She licked her lips, her eyes fixed on the outline of my soft cock in my pants. “Me too,” she said lustily.

One short drive later, we were pulling up in front of the restaurant. The sandstone-brick exterior, paired with vines spilling from windowsill gardens, really made the building feel like something out of Southern Italy. No wonder, then, that it was overflowing with the finely dressed well-to-do members of Segian Society. Mila was quite impressed, I could tell.

I tossed the keys of the Rolls to the valet. Then I took Mila’s hand, leading her into the restaurant. The crowd waiting to be seated parted as I passed. These people all recognized me; no one who was anyone in Segia wouldn’t recognize the Segeste heir. Some greetings were called after me, and I sent a few nods back. I blended perfectly naturally into this setting. Mila, on the other hand, stuck out somewhat. She shifted uncomfortably at the looks she was getting. See, this wasn’t the kind of restaurant you would usually take a casual hoe to. Because of the expense and the social aspect, only a wife or important mistress who could navigate society was brought here on a date. The waitresses were available if you just wanted to fuck, after all. And the clothes worn by wives and mistresses to this place were somewhat more elegant than what Mila had on, though still plenty revealing. Intricate dresses of expensive fabric that almost succeeded in distracting from the fact that they left nothing to the imagination.

I put my arm possessively around Mila’s shoulder, and the eyes averted. I was never one to conform to Society. Society conformed to me. And anyway, most of the people who had been judging Mila were just bitches who wished they were in her place.

I greeted the hostess in her whorish uniform, and she immediately led us through the restaurant. As we walked, I was satisfied to note the sex going on at some of the tables, with both waitresses and dates. I was sure there was more going on in the back rooms, but if the changes I had brought about had penetrated even this bastion of the elite, they truly had been a success.

Our table was on an elevated alcove on the second floor balcony, a spot overlooking the whole restaurant. A place of power, reserved for only the most select of customers. My usual table. There were curtains that could provide some privacy, but I decided not to have them drawn. Let them watch. It would make things more fun with Mila.

I graciously pulled out my date’s chair for her, still playing the perfect gentleman. As I took my own seat, I noticed her confused look at the vast array of silverware. I suppressed my chuckle. “So, Mila, what do you do for a living?”

“I’m a receptionist at a law firm downtown.” Her tone suggested she was embarrassed to admit to such a lowly position, surrounded by all these powerful people. It was foolish of her. A receptionist had it pretty good, given that most men had probably already fucked one of their sluts before coming to work, and had their secretaries to look forward to in their offices. Receptionists were still paid next to nothing, of course. Besides, I suspected she would find the position of mistress to one of these lesser elites to not quite live up to her expectations. Their sluts at home were just as looked down upon as the ones they saw at work. They just got nicer clothes.

“I suppose it probably isn’t much of a secret what my career is,” I replied.

She perked up, glad the topic had moved on. “That’s right! I heard you’re the new Council Chairman!”

“Indeed.”

Just then, the waitress arrived to take our orders. Mila did not get her own, given that she was a woman. “What can I get for you, sir?” She asked brightly. A sexy bitch, though not quite on the level of Mila.

“I’ll take a scotch on the rocks, your Macallan. And a Carpaccio. Also, a bottle of your best champagne. Oh, and she’ll have a Tagliatelle.” My voice brooked no argument, sending the waitress right on her way with a ‘Yes, sir’.

I didn’t actually care what Mila ate, or have any particular taste for the dish I had ordered for her. I was just making sure she knew who was in charge around here. And I wanted to test her reaction. She did not disappoint on that front, not voicing a word of complaint.

Barely a moment later, the champagne arrived, and the conversation began to flow. I dominated it, but she managed to follow along, knowing what to say and how to react. More importantly, she knew how to listen. I didn’t want a complete bimbo who couldn’t even follow a conversation. I was planning to spend some time around my mistresses, and not every second would be spent fucking them.

We talked about various things. My world tour, fitness, my thoughts on the people around us. None of it was very intellectual or worthwhile, really. She was a woman, after all, and didn’t have the mental capacity to understand more complex topics. But it filled the time, and allowed me to get a better picture of her, and to subtly manipulate her to better suit my desires. It also allowed her to ingest a rather significant amount of ****. She was clearly enjoying this taste of the finer things in life. I just sipped my whiskey.

It wasn’t long before the waitress returned with our food. I ordered another bottle of champagne from her. As she walked away, I made sure to obviously fix my eyes on her swaying hips and exposed ass. Mila noticed, too drunk to realize she was glowering.

She didn’t take long with that bottle, either. When the waitress brought a third, I copped a feel of her tits. Mila was positively scowling at that point. Once the waitress left, she twirled her hair, batting her eyelashes flirtatiously.

In her best drunken attempt at sensuality, she said, “You should stop by my law firm. There’s all sorts of things I could show you!” As she spoke, she leaned down unsubtly to give me a look at her valley of cleavage.

She was not much of a seductress, at least while drunk. Oh, sure, it got the blood pumping a bit. But offering sex at her office was not especially exciting. I could bend her over the table and fuck her ass if I wanted to, though letting her whore herself out to me all on her own was more satisfying. No, the whole thing was an art. An art she did not understand.

That hardly mattered, though. When the waitress came back with Mila’s dessert, I gave her ass a firm slap as she walked away. When I turned back, Mila had her tits out. She had been looking around nervously at the other patrons, worried to be seen as a whore. Her fears were well founded, though it wasn’t as if plenty of the women at the other tables weren’t behaving in a similar manner. But when she noticed that I was looking, all those thoughts fled her mind. Her flush deepened, though from arousal rather than embarrassment. As my eyes traced her lovely tits, she could hardly have been more turned on. In fact, a certain sharpening of my stare, and voila! She had a mini orgasm. This was not a night she would soon forget.

Still, when I rose to my feet, she was just conscious enough to cover herself. I held out my hand, helping her rise. She gave me a lovely smile. “I just wanted to give you a little treat,” she giggled. “For knowing how to treat a lady.”

“One of my best qualities. I’m glad you know how to behave like one.” Another blush.

I led her out of the restaurant, ignoring the prying eyes that followed us. My car was waiting by the curb. The drive to Mila’s apartment proceeded mostly in silence, filled only by Steel Panther’s classic “That’s What Girls Are For”. When we arrived at her apartment, she turned to me and gave me a hesitant kiss before she opened the door. As she clambered out, I copped a feel of her ass.